TW201038559A - Hepatitis C virus inhibitors - Google Patents

Hepatitis C virus inhibitors Download PDF

Info

Publication number: TW201038559A
Authority: TW; Taiwan
Prior art keywords: rti; mmol; cap; hcv; etoac
Prior art date: 2009-04-09

Application number

TW099109167A

Other languages

English (en)

Chinese (zh)

Inventor

Makonen Belema

John F Kadow

Original Assignee

Bristol Myers Squibb Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2009-04-09

Filing date

2010-03-26

Publication date

2010-11-01

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=42244128&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=TW201038559(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2010-03-26 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

2010-11-01 Publication of TW201038559A publication Critical patent/TW201038559A/zh

Links

241000711549 Hepacivirus C Species 0.000 title abstract description 54
239000003112 inhibitor Substances 0.000 title description 23
239000000203 mixture Substances 0.000 claims abstract description 201
150000001875 compounds Chemical class 0.000 claims abstract description 138
208000015181 infectious disease Diseases 0.000 claims abstract description 13
-1 (methoxy)amino Chemical group 0.000 claims description 83
125000000217 alkyl group Chemical group 0.000 claims description 50
150000003839 salts Chemical class 0.000 claims description 50
239000002253 acid Substances 0.000 claims description 34
229940079322 interferon Drugs 0.000 claims description 32
108010050904 Interferons Proteins 0.000 claims description 31
102000014150 Interferons Human genes 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 31
229910052739 hydrogen Inorganic materials 0.000 claims description 31
125000000623 heterocyclic group Chemical group 0.000 claims description 28
239000003814 drug Substances 0.000 claims description 25
239000011734 sodium Substances 0.000 claims description 25
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 20
150000002148 esters Chemical class 0.000 claims description 20
239000003795 chemical substances by application Substances 0.000 claims description 14
125000003710 aryl alkyl group Chemical group 0.000 claims description 13
230000000694 effects Effects 0.000 claims description 12
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 12
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 12
101800001014 Non-structural protein 5A Proteins 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
239000002777 nucleoside Substances 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 8
108091032973 (ribonucleotides)n+m Proteins 0.000 claims description 7
DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims description 7
229960003805 amantadine Drugs 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
101710200424 Inosine-5'-monophosphate dehydrogenase Proteins 0.000 claims description 6
108010078049 Interferon alpha-2 Proteins 0.000 claims description 6
102100039350 Interferon alpha-7 Human genes 0.000 claims description 5
108010047761 Interferon-alpha Proteins 0.000 claims description 5
102000006992 Interferon-alpha Human genes 0.000 claims description 5
108010006035 Metalloproteases Proteins 0.000 claims description 5
102000005741 Metalloproteases Human genes 0.000 claims description 5
108060004795 Methyltransferase Proteins 0.000 claims description 5
101800001019 Non-structural protein 4B Proteins 0.000 claims description 5
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 5
238000011161 development Methods 0.000 claims description 5
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 4
108010022999 Serine Proteases Proteins 0.000 claims description 4
102000012479 Serine Proteases Human genes 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
230000036755 cellular response Effects 0.000 claims description 4
210000002443 helper t lymphocyte Anatomy 0.000 claims description 4
YRHYCMZPEVDGFQ-UHFFFAOYSA-N n-decanoic acid methyl ester Natural products CCCCCCCCCC(=O)OC YRHYCMZPEVDGFQ-UHFFFAOYSA-N 0.000 claims description 4
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 4
OJQARJSTQMLUFB-UHFFFAOYSA-N amino decanoate Chemical compound CCCCCCCCCC(=O)ON OJQARJSTQMLUFB-UHFFFAOYSA-N 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 3
230000002452 interceptive effect Effects 0.000 claims description 3
JINGUCXQUOKWKH-UHFFFAOYSA-N 2-aminodecanoic acid Chemical compound CCCCCCCCC(N)C(O)=O JINGUCXQUOKWKH-UHFFFAOYSA-N 0.000 claims description 2
125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
210000003969 blast cell Anatomy 0.000 claims description 2
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
MWDWULMCMBQTEV-UHFFFAOYSA-N dimethyl 3,4-dimethylbenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=C(C)C(C)=C1C(=O)OC MWDWULMCMBQTEV-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
239000002689 soil Substances 0.000 claims description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
239000002348 inosinate dehydrogenase inhibitor Substances 0.000 claims 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
230000002889 sympathetic effect Effects 0.000 claims 2
NFOQRIXSEYVCJP-UHFFFAOYSA-N 2-propoxycarbonylbenzoic acid Chemical compound CCCOC(=O)C1=CC=CC=C1C(O)=O NFOQRIXSEYVCJP-UHFFFAOYSA-N 0.000 claims 1
108020005544 Antisense RNA Proteins 0.000 claims 1
VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 claims 1
LJZDFZSLLYVEAM-UHFFFAOYSA-N carbamic acid;guanidine Chemical compound NC(N)=N.NC(O)=O LJZDFZSLLYVEAM-UHFFFAOYSA-N 0.000 claims 1
239000003184 complementary RNA Substances 0.000 claims 1
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims 1
ROPYKWJBZRXADC-UHFFFAOYSA-N dimethyl 3,4-diaminobenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=C(N)C(N)=C1C(=O)OC ROPYKWJBZRXADC-UHFFFAOYSA-N 0.000 claims 1
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims 1
125000001475 halogen functional group Chemical group 0.000 claims 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
210000003296 saliva Anatomy 0.000 claims 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 1
229960000281 trometamol Drugs 0.000 claims 1
238000000034 method Methods 0.000 abstract description 79
238000011282 treatment Methods 0.000 abstract description 16
239000008194 pharmaceutical composition Substances 0.000 abstract description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 473
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 270
235000019439 ethyl acetate Nutrition 0.000 description 216
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 183
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 170
229910001868 water Inorganic materials 0.000 description 135
239000000243 solution Substances 0.000 description 118
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 114
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 102
238000005481 NMR spectroscopy Methods 0.000 description 99
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 89
238000004458 analytical method Methods 0.000 description 79
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
239000011541 reaction mixture Substances 0.000 description 64
239000002904 solvent Substances 0.000 description 62
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 58
239000007787 solid Substances 0.000 description 58
238000005160 1H NMR spectroscopy Methods 0.000 description 51
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 47
239000003921 oil Substances 0.000 description 45
235000019198 oils Nutrition 0.000 description 45
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 43
238000006243 chemical reaction Methods 0.000 description 43
238000000746 purification Methods 0.000 description 42
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
239000012044 organic layer Substances 0.000 description 35
238000003756 stirring Methods 0.000 description 35
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
239000000047 product Substances 0.000 description 34
239000000725 suspension Substances 0.000 description 34
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 32
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 32
125000003118 aryl group Chemical group 0.000 description 32
230000000840 anti-viral effect Effects 0.000 description 30
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 29
239000013058 crude material Substances 0.000 description 28
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
239000012267 brine Substances 0.000 description 27
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 27
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 26
238000002360 preparation method Methods 0.000 description 26
239000000463 material Substances 0.000 description 25
239000003039 volatile agent Substances 0.000 description 23
229930182558 Sterol Natural products 0.000 description 22
OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 22
150000003432 sterols Chemical class 0.000 description 22
235000003702 sterols Nutrition 0.000 description 22
101150041968 CDC13 gene Proteins 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 20
239000000543 intermediate Substances 0.000 description 20
230000015572 biosynthetic process Effects 0.000 description 19
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 19
239000006260 foam Substances 0.000 description 19
239000012074 organic phase Substances 0.000 description 18
125000001424 substituent group Chemical group 0.000 description 18
238000003786 synthesis reaction Methods 0.000 description 18
239000010410 layer Substances 0.000 description 17
229910052757 nitrogen Inorganic materials 0.000 description 17
230000002829 reductive effect Effects 0.000 description 17
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 16
101800001554 RNA-directed RNA polymerase Proteins 0.000 description 16
229960000583 acetic acid Drugs 0.000 description 16
239000002585 base Substances 0.000 description 16
238000001816 cooling Methods 0.000 description 16
239000000706 filtrate Substances 0.000 description 16
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 16
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 14
238000004128 high performance liquid chromatography Methods 0.000 description 14
229910052943 magnesium sulfate Inorganic materials 0.000 description 14
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 14
239000000843 powder Substances 0.000 description 14
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 13
239000008346 aqueous phase Substances 0.000 description 13
239000005457 ice water Substances 0.000 description 13
108010026228 mRNA guanylyltransferase Proteins 0.000 description 13
229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
150000001412 amines Chemical class 0.000 description 12
201000010099 disease Diseases 0.000 description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 12
238000004007 reversed phase HPLC Methods 0.000 description 12
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 11
239000007788 liquid Substances 0.000 description 11
229920006395 saturated elastomer Polymers 0.000 description 11
238000000926 separation method Methods 0.000 description 11
239000007858 starting material Substances 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 10
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
238000003818 flash chromatography Methods 0.000 description 10
238000009472 formulation Methods 0.000 description 10
239000007789 gas Substances 0.000 description 10
239000012071 phase Substances 0.000 description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 9
239000011575 calcium Substances 0.000 description 9
238000004364 calculation method Methods 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
239000007924 injection Substances 0.000 description 9
238000002347 injection Methods 0.000 description 9
150000005331 phenylglycines Chemical class 0.000 description 9
238000002953 preparative HPLC Methods 0.000 description 9
230000002441 reversible effect Effects 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
239000003826 tablet Substances 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
150000001413 amino acids Chemical group 0.000 description 8
239000000052 vinegar Substances 0.000 description 8
235000021419 vinegar Nutrition 0.000 description 8
229960000549 4-dimethylaminophenol Drugs 0.000 description 7
229940122055 Serine protease inhibitor Drugs 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
229940024606 amino acid Drugs 0.000 description 7
239000012230 colorless oil Substances 0.000 description 7
239000008241 heterogeneous mixture Substances 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
108090000623 proteins and genes Proteins 0.000 description 7
239000003001 serine protease inhibitor Substances 0.000 description 7
229910000029 sodium carbonate Inorganic materials 0.000 description 7
208000024891 symptom Diseases 0.000 description 7
239000003643 water by type Substances 0.000 description 7
101710179624 Antiviral serine protease Proteins 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
101710144111 Non-structural protein 3 Proteins 0.000 description 6
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
235000001014 amino acid Nutrition 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
239000012298 atmosphere Substances 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
125000004093 cyano group Chemical group *C#N 0.000 description 6
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 6
150000003840 hydrochlorides Chemical class 0.000 description 6
239000002955 immunomodulating agent Substances 0.000 description 6
229940121354 immunomodulator Drugs 0.000 description 6
230000002584 immunomodulator Effects 0.000 description 6
239000012535 impurity Substances 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
150000002576 ketones Chemical class 0.000 description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
229910000069 nitrogen hydride Inorganic materials 0.000 description 6
230000003287 optical effect Effects 0.000 description 6
235000019260 propionic acid Nutrition 0.000 description 6
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 5
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 5
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 5
108010010803 Gelatin Proteins 0.000 description 5
ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 5
229940123066 Polymerase inhibitor Drugs 0.000 description 5
206010036790 Productive cough Diseases 0.000 description 5
241000700605 Viruses Species 0.000 description 5
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 5
230000008901 benefit Effects 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
238000000576 coating method Methods 0.000 description 5
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 5
239000008273 gelatin Substances 0.000 description 5
229920000159 gelatin Polymers 0.000 description 5
235000019322 gelatine Nutrition 0.000 description 5
235000011852 gelatine desserts Nutrition 0.000 description 5
125000001188 haloalkyl group Chemical group 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
210000003802 sputum Anatomy 0.000 description 5
208000024794 sputum Diseases 0.000 description 5
235000000346 sugar Nutrition 0.000 description 5
238000002560 therapeutic procedure Methods 0.000 description 5
OWJLCJLXRSNPJK-GFCCVEGCSA-N (2r)-2-(cyclopentylcarbamoylamino)-2-phenylacetic acid Chemical compound N([C@@H](C(=O)O)C=1C=CC=CC=1)C(=O)NC1CCCC1 OWJLCJLXRSNPJK-GFCCVEGCSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
229960003767 alanine Drugs 0.000 description 4
150000001336 alkenes Chemical group 0.000 description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
125000004448 alkyl carbonyl group Chemical group 0.000 description 4
125000005129 aryl carbonyl group Chemical group 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
239000008280 blood Substances 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000011248 coating agent Substances 0.000 description 4
239000012043 crude product Substances 0.000 description 4
238000001514 detection method Methods 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
238000009826 distribution Methods 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000000975 dye Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000008187 granular material Substances 0.000 description 4
125000004438 haloalkoxy group Chemical group 0.000 description 4
239000003018 immunosuppressive agent Substances 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
238000012544 monitoring process Methods 0.000 description 4
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
125000004433 nitrogen atom Chemical group N* 0.000 description 4
239000006072 paste Substances 0.000 description 4
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 4
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
235000018102 proteins Nutrition 0.000 description 4
102000004169 proteins and genes Human genes 0.000 description 4
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
239000002002 slurry Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
230000003612 virological effect Effects 0.000 description 4
JLHJCPDYFXYNFG-SECBINFHSA-N (2r)-2-(ethylamino)-2-phenylacetic acid Chemical compound CCN[C@@H](C(O)=O)C1=CC=CC=C1 JLHJCPDYFXYNFG-SECBINFHSA-N 0.000 description 3
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 3
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 3
229930105110 Cyclosporin A Natural products 0.000 description 3
108010036949 Cyclosporine Proteins 0.000 description 3
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 3
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
101000933374 Gallus gallus Brain-specific homeobox/POU domain protein 3 Proteins 0.000 description 3
239000007821 HATU Substances 0.000 description 3
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 3
239000007832 Na2SO4 Substances 0.000 description 3
VONGZNXBKCOUHB-UHFFFAOYSA-N Phenylmethyl butanoate Chemical compound CCCC(=O)OCC1=CC=CC=C1 VONGZNXBKCOUHB-UHFFFAOYSA-N 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
208000003251 Pruritus Diseases 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
125000002619 bicyclic group Chemical group 0.000 description 3
LHHCSNFAOIFYRV-DOVBMPENSA-N boceprevir Chemical compound O=C([C@@H]1[C@@H]2[C@@H](C2(C)C)CN1C(=O)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C)NC(C(=O)C(N)=O)CC1CCC1 LHHCSNFAOIFYRV-DOVBMPENSA-N 0.000 description 3
KFCUPNHUPHDVJC-UHFFFAOYSA-N bromine azide Chemical compound BrN=[N+]=[N-] KFCUPNHUPHDVJC-UHFFFAOYSA-N 0.000 description 3
GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
239000003729 cation exchange resin Substances 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
229960001265 ciclosporin Drugs 0.000 description 3
230000008878 coupling Effects 0.000 description 3
238000010168 coupling process Methods 0.000 description 3
238000005859 coupling reaction Methods 0.000 description 3
239000006071 cream Substances 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
239000007884 disintegrant Substances 0.000 description 3
239000006196 drop Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
239000000284 extract Substances 0.000 description 3
XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000001307 helium Substances 0.000 description 3
229910052734 helium Inorganic materials 0.000 description 3
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
238000006317 isomerization reaction Methods 0.000 description 3
125000000468 ketone group Chemical group 0.000 description 3
239000000314 lubricant Substances 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 3
150000004702 methyl esters Chemical class 0.000 description 3
238000002156 mixing Methods 0.000 description 3
230000035772 mutation Effects 0.000 description 3
150000003833 nucleoside derivatives Chemical class 0.000 description 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
150000002923 oximes Chemical class 0.000 description 3
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
229960003424 phenylacetic acid Drugs 0.000 description 3
239000003279 phenylacetic acid Substances 0.000 description 3
WNMODAROKMEXRP-UHFFFAOYSA-N propanoyl decanoate Chemical compound CCCCCCCCCC(=O)OC(=O)CC WNMODAROKMEXRP-UHFFFAOYSA-N 0.000 description 3
239000013557 residual solvent Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
238000012360 testing method Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 3
238000005406 washing Methods 0.000 description 3
239000001993 wax Substances 0.000 description 3
JCWUTEGWHABTTF-SECBINFHSA-N (2r)-2-(dimethylazaniumyl)-2-(2-fluorophenyl)acetate Chemical compound CN(C)[C@@H](C(O)=O)C1=CC=CC=C1F JCWUTEGWHABTTF-SECBINFHSA-N 0.000 description 2
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical compound C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
FOZVXADQAHVUSV-UHFFFAOYSA-N 1-bromo-2-(2-bromoethoxy)ethane Chemical compound BrCCOCCBr FOZVXADQAHVUSV-UHFFFAOYSA-N 0.000 description 2
ABEXEQSGABRUHS-UHFFFAOYSA-N 16-methylheptadecyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C ABEXEQSGABRUHS-UHFFFAOYSA-N 0.000 description 2
238000004293 19F NMR spectroscopy Methods 0.000 description 2
FRUWMYWEARDNTC-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-indole Chemical compound C1C=CC=C2NCCC21 FRUWMYWEARDNTC-UHFFFAOYSA-N 0.000 description 2
ROZCIVXTLACYNY-UHFFFAOYSA-N 2,3,4,5,6-pentafluoro-n-(3-fluoro-4-methoxyphenyl)benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC=C1NS(=O)(=O)C1=C(F)C(F)=C(F)C(F)=C1F ROZCIVXTLACYNY-UHFFFAOYSA-N 0.000 description 2
RPTRFSADOICSSK-UHFFFAOYSA-N 2-(2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1F RPTRFSADOICSSK-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 description 2
UPGATMBHQQONPH-UHFFFAOYSA-N 2-aminooxycarbonylbenzoic acid Chemical compound NOC(=O)C1=CC=CC=C1C(O)=O UPGATMBHQQONPH-UHFFFAOYSA-N 0.000 description 2
WAKFRZBXTKUFIW-UHFFFAOYSA-N 2-bromo-2-phenylacetic acid Chemical compound OC(=O)C(Br)C1=CC=CC=C1 WAKFRZBXTKUFIW-UHFFFAOYSA-N 0.000 description 2
RQPNXPWEGVCPCX-UHFFFAOYSA-N 3-sulfanylbutanoic acid Chemical compound CC(S)CC(O)=O RQPNXPWEGVCPCX-UHFFFAOYSA-N 0.000 description 2
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
239000005695 Ammonium acetate Substances 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
JGLJBVOECVUSCR-UHFFFAOYSA-N C(C)OC1(CC1)OCCCCCCCCCCCCCCCCCCCCCCC Chemical compound C(C)OC1(CC1)OCCCCCCCCCCCCCCCCCCCCCCC JGLJBVOECVUSCR-UHFFFAOYSA-N 0.000 description 2
XFCSCWCSROMXOR-UHFFFAOYSA-N C(C1=CC=CC=C1)OC(C(C)NC(=O)OCCCCCCCCC)=O Chemical compound C(C1=CC=CC=C1)OC(C(C)NC(=O)OCCCCCCCCC)=O XFCSCWCSROMXOR-UHFFFAOYSA-N 0.000 description 2
101100326791 Caenorhabditis elegans cap-2 gene Proteins 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 2
229940124186 Dehydrogenase inhibitor Drugs 0.000 description 2
241000710781 Flaviviridae Species 0.000 description 2
229940126656 GS-4224 Drugs 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
101000793686 Homo sapiens Azurocidin Proteins 0.000 description 2
241000764238 Isis Species 0.000 description 2
QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 2
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 2
UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 description 2
ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 2
229930182821 L-proline Natural products 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 2
AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
101800001020 Non-structural protein 4A Proteins 0.000 description 2
108700026244 Open Reading Frames Proteins 0.000 description 2
235000019502 Orange oil Nutrition 0.000 description 2
240000007594 Oryza sativa Species 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
108010076039 Polyproteins Proteins 0.000 description 2
241001085205 Prenanthella exigua Species 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
101800001838 Serine protease/helicase NS3 Proteins 0.000 description 2
229910004298 SiO 2 Inorganic materials 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
235000021355 Stearic acid Nutrition 0.000 description 2
239000005864 Sulphur Substances 0.000 description 2
239000004473 Threonine Substances 0.000 description 2
108010078233 Thymalfasin Proteins 0.000 description 2
108700022715 Viral Proteases Proteins 0.000 description 2
JBPUGFODGPKTDW-SFHVURJKSA-N [(3s)-oxolan-3-yl] n-[[3-[[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoylamino]phenyl]methyl]carbamate Chemical compound C=1C=C(C=2OC=NC=2)C(OC)=CC=1NC(=O)NC(C=1)=CC=CC=1CNC(=O)O[C@H]1CCOC1 JBPUGFODGPKTDW-SFHVURJKSA-N 0.000 description 2
IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 2
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000008186 active pharmaceutical agent Substances 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 description 2
208000026935 allergic disease Diseases 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
235000019257 ammonium acetate Nutrition 0.000 description 2
229940043376 ammonium acetate Drugs 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
239000011609 ammonium molybdate Substances 0.000 description 2
235000018660 ammonium molybdate Nutrition 0.000 description 2
APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 2
229940010552 ammonium molybdate Drugs 0.000 description 2
229910052921 ammonium sulfate Inorganic materials 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
238000003556 assay Methods 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
150000001558 benzoic acid derivatives Chemical class 0.000 description 2
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
229960000074 biopharmaceutical Drugs 0.000 description 2
229960000517 boceprevir Drugs 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
108010079344 calcyclin-associated protein 50 Proteins 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
230000008859 change Effects 0.000 description 2
238000012512 characterization method Methods 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
235000008504 concentrate Nutrition 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
230000001143 conditioned effect Effects 0.000 description 2
238000011109 contamination Methods 0.000 description 2
229910000366 copper(II) sulfate Inorganic materials 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
ZVTDLPBHTSMEJZ-JSZLBQEHSA-N danoprevir Chemical compound O=C([C@@]12C[C@H]1\C=C/CCCCC[C@@H](C(N1C[C@@H](C[C@H]1C(=O)N2)OC(=O)N1CC2=C(F)C=CC=C2C1)=O)NC(=O)OC(C)(C)C)NS(=O)(=O)C1CC1 ZVTDLPBHTSMEJZ-JSZLBQEHSA-N 0.000 description 2
238000006193 diazotization reaction Methods 0.000 description 2
YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 2
238000006073 displacement reaction Methods 0.000 description 2
238000010494 dissociation reaction Methods 0.000 description 2
230000005593 dissociations Effects 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
239000000835 fiber Substances 0.000 description 2
238000011049 filling Methods 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
239000012458 free base Substances 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
239000000499 gel Substances 0.000 description 2
230000003179 granulation Effects 0.000 description 2
238000005469 granulation Methods 0.000 description 2
PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
125000006517 heterocyclyl carbonyl group Chemical group 0.000 description 2
229960001340 histamine Drugs 0.000 description 2
102000043635 human AZU1 Human genes 0.000 description 2
108010036050 human cationic antimicrobial protein 57 Proteins 0.000 description 2
102000011834 human cationic antimicrobial protein 57 Human genes 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
238000005417 image-selected in vivo spectroscopy Methods 0.000 description 2
229960003444 immunosuppressant agent Drugs 0.000 description 2
230000001861 immunosuppressant effect Effects 0.000 description 2
229940125721 immunosuppressive agent Drugs 0.000 description 2
238000012739 integrated shape imaging system Methods 0.000 description 2
229940065638 intron a Drugs 0.000 description 2
239000003456 ion exchange resin Substances 0.000 description 2
229920003303 ion-exchange polymer Polymers 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
235000013336 milk Nutrition 0.000 description 2
239000008267 milk Substances 0.000 description 2
210000004080 milk Anatomy 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
125000002950 monocyclic group Chemical group 0.000 description 2
229960005181 morphine Drugs 0.000 description 2
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
YLYBTZIQSIBWLI-UHFFFAOYSA-N octyl acetate Chemical compound CCCCCCCCOC(C)=O YLYBTZIQSIBWLI-UHFFFAOYSA-N 0.000 description 2
239000010502 orange oil Substances 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
230000037361 pathway Effects 0.000 description 2
108010092853 peginterferon alfa-2a Proteins 0.000 description 2
108010092851 peginterferon alfa-2b Proteins 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
229940049953 phenylacetate Drugs 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
230000002265 prevention Effects 0.000 description 2
229960002429 proline Drugs 0.000 description 2
230000002035 prolonged effect Effects 0.000 description 2
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 2
230000009467 reduction Effects 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
229910052702 rhenium Inorganic materials 0.000 description 2
235000009566 rice Nutrition 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
238000009097 single-agent therapy Methods 0.000 description 2
PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 2
235000010378 sodium ascorbate Nutrition 0.000 description 2
229960005055 sodium ascorbate Drugs 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000008117 stearic acid Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
239000001384 succinic acid Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
229940095064 tartrate Drugs 0.000 description 2
BBAWEDCPNXPBQM-GDEBMMAJSA-N telaprevir Chemical compound N([C@H](C(=O)N[C@H](C(=O)N1C[C@@H]2CCC[C@@H]2[C@H]1C(=O)N[C@@H](CCC)C(=O)C(=O)NC1CC1)C(C)(C)C)C1CCCCC1)C(=O)C1=CN=CC=N1 BBAWEDCPNXPBQM-GDEBMMAJSA-N 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
229960002898 threonine Drugs 0.000 description 2
NZVYCXVTEHPMHE-ZSUJOUNUSA-N thymalfasin Chemical compound CC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O NZVYCXVTEHPMHE-ZSUJOUNUSA-N 0.000 description 2
229960004231 thymalfasin Drugs 0.000 description 2
230000007704 transition Effects 0.000 description 2
238000013519 translation Methods 0.000 description 2
150000003852 triazoles Chemical class 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
230000029812 viral genome replication Effects 0.000 description 2
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
JLVPLCVIBPZJQG-UHFFFAOYSA-N (1-carboxy-1-phenylethyl)azanium;chloride Chemical compound Cl.OC(=O)C(N)(C)C1=CC=CC=C1 JLVPLCVIBPZJQG-UHFFFAOYSA-N 0.000 description 1
IYLGZMTXKJYONK-ACLXAEORSA-N (12s,15r)-15-hydroxy-11,16-dioxo-15,20-dihydrosenecionan-12-yl acetate Chemical compound O1C(=O)[C@](CC)(O)C[C@@H](C)[C@](C)(OC(C)=O)C(=O)OCC2=CCN3[C@H]2[C@H]1CC3 IYLGZMTXKJYONK-ACLXAEORSA-N 0.000 description 1
BTLCATHEBLRUAV-ZCFIWIBFSA-N (2r)-2-(diethylamino)-3-hydroxypropanoic acid Chemical compound CCN(CC)[C@H](CO)C(O)=O BTLCATHEBLRUAV-ZCFIWIBFSA-N 0.000 description 1
NLPIZOSHELQGNL-SECBINFHSA-N (2r)-2-(dimethylcarbamoylamino)-2-phenylacetic acid Chemical compound CN(C)C(=O)N[C@@H](C(O)=O)C1=CC=CC=C1 NLPIZOSHELQGNL-SECBINFHSA-N 0.000 description 1
JKFYKCYQEWQPTM-SSDOTTSWSA-N (2r)-2-amino-2-(4-fluorophenyl)acetic acid Chemical compound OC(=O)[C@H](N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-SSDOTTSWSA-N 0.000 description 1
SIHHATSLPITFFO-OGFXRTJISA-N (2r)-2-amino-2-phenylacetic acid;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.OC(=O)[C@H](N)C1=CC=CC=C1 SIHHATSLPITFFO-OGFXRTJISA-N 0.000 description 1
IAZPUJDTYUZJMI-OGFXRTJISA-N (2r)-2-amino-2-phenylacetic acid;hydrochloride Chemical compound Cl.OC(=O)[C@H](N)C1=CC=CC=C1 IAZPUJDTYUZJMI-OGFXRTJISA-N 0.000 description 1
YHZCTZGJKHNVQY-LURJTMIESA-N (2s)-2-(diethylazaniumyl)propanoate Chemical compound CCN(CC)[C@@H](C)C(O)=O YHZCTZGJKHNVQY-LURJTMIESA-N 0.000 description 1
TXJCSRZHJCNEBF-ZETCQYMHSA-N (2s)-2-amino-4-(diethylamino)butanoic acid Chemical compound CCN(CC)CC[C@H](N)C(O)=O TXJCSRZHJCNEBF-ZETCQYMHSA-N 0.000 description 1
XLZJPHKIECMDPG-LURJTMIESA-N (2s)-2-azaniumyl-2-(oxan-4-yl)acetate Chemical compound OC(=O)[C@@H](N)C1CCOCC1 XLZJPHKIECMDPG-LURJTMIESA-N 0.000 description 1
ZIWHMENIDGOELV-DMTCNVIQSA-N (2s,4r)-4-fluoropyrrolidin-1-ium-2-carboxylate Chemical compound OC(=O)[C@@H]1C[C@@H](F)CN1 ZIWHMENIDGOELV-DMTCNVIQSA-N 0.000 description 1
SCVHJVCATBPIHN-SJCJKPOMSA-N (3s)-3-[[(2s)-2-[[2-(2-tert-butylanilino)-2-oxoacetyl]amino]propanoyl]amino]-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoic acid Chemical compound N([C@@H](C)C(=O)N[C@@H](CC(O)=O)C(=O)COC=1C(=C(F)C=C(F)C=1F)F)C(=O)C(=O)NC1=CC=CC=C1C(C)(C)C SCVHJVCATBPIHN-SJCJKPOMSA-N 0.000 description 1
JXDNUMOTWHZSCB-XMTZKCFKSA-N (3s)-3-acetamido-4-[[(2s)-3-carboxy-1-[[(2s,3s)-1-[[(2s)-1-[(2s)-2-[[(1r)-1-carboxy-2-sulfanylethyl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-oxobutanoic acid Chemical group OC(=O)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CS)C(O)=O JXDNUMOTWHZSCB-XMTZKCFKSA-N 0.000 description 1
JBSNALXXNTWUEC-SFQUDFHCSA-N (e)-3-[4-[[1-[(3-cyclopentyl-1-methyl-2-pyridin-2-ylindole-6-carbonyl)amino]cyclobutanecarbonyl]amino]phenyl]prop-2-enoic acid Chemical compound C12=CC=C(C(=O)NC3(CCC3)C(=O)NC=3C=CC(\C=C\C(O)=O)=CC=3)C=C2N(C)C(C=2N=CC=CC=2)=C1C1CCCC1 JBSNALXXNTWUEC-SFQUDFHCSA-N 0.000 description 1
108010030583 (melle-4)cyclosporin Proteins 0.000 description 1
102000040650 (ribonucleotides)n+m Human genes 0.000 description 1
UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 description 1
ATWLRNODAYAMQS-UHFFFAOYSA-N 1,1-dibromopropane Chemical compound CCC(Br)Br ATWLRNODAYAMQS-UHFFFAOYSA-N 0.000 description 1
VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
NPWSCICJCAGHOX-UHFFFAOYSA-N 1,3-dichloro-5-ethoxyisoquinoline Chemical compound N1=C(Cl)C=C2C(OCC)=CC=CC2=C1Cl NPWSCICJCAGHOX-UHFFFAOYSA-N 0.000 description 1
BRGZEQXWZWBPJH-UHFFFAOYSA-N 1,3-dichloroisoquinoline Chemical compound C1=CC=C2C(Cl)=NC(Cl)=CC2=C1 BRGZEQXWZWBPJH-UHFFFAOYSA-N 0.000 description 1
ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
NRBSVPXPMBQUGX-UHFFFAOYSA-N 1,7-dichloroisoquinoline Chemical compound C1=CN=C(Cl)C2=CC(Cl)=CC=C21 NRBSVPXPMBQUGX-UHFFFAOYSA-N 0.000 description 1
WXAVSTZWKNIWCN-UHFFFAOYSA-N 1-(1-phenylethoxy)ethylbenzene Chemical compound C=1C=CC=CC=1C(C)OC(C)C1=CC=CC=C1 WXAVSTZWKNIWCN-UHFFFAOYSA-N 0.000 description 1
OCKPEBVTWOEXDC-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxycarbonyl]-2,3-dihydroisoindol-2-ium-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC(C)(C)C)(C(O)=O)NCC2=C1 OCKPEBVTWOEXDC-UHFFFAOYSA-N 0.000 description 1
IWUCXVSUMQZMFG-RGDLXGNYSA-N 1-[(2s,3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)N)N=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 IWUCXVSUMQZMFG-RGDLXGNYSA-N 0.000 description 1
GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
KKKDZZRICRFGSD-UHFFFAOYSA-N 1-benzylimidazole Chemical compound C1=CN=CN1CC1=CC=CC=C1 KKKDZZRICRFGSD-UHFFFAOYSA-N 0.000 description 1
MONVOHRDPXYPGQ-UHFFFAOYSA-N 1-diphenylphosphanylpentyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(CCCC)P(C=1C=CC=CC=1)C1=CC=CC=C1 MONVOHRDPXYPGQ-UHFFFAOYSA-N 0.000 description 1
XFEWMFDVBLLXFE-UHFFFAOYSA-N 1-isocyanatodecane Chemical compound CCCCCCCCCCN=C=O XFEWMFDVBLLXFE-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
XAQPFUUTSNMMQH-UHFFFAOYSA-N 10,10,10-trifluorodecane-1-sulfonic acid Chemical compound FC(CCCCCCCCCS(=O)(=O)O)(F)F XAQPFUUTSNMMQH-UHFFFAOYSA-N 0.000 description 1
WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical class CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 1
XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 description 1
KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical compound C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 description 1
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
FXHYAXBIUKRLLT-UHFFFAOYSA-N 2-(decylazaniumyl)acetate Chemical compound CCCCCCCCCCNCC(O)=O FXHYAXBIUKRLLT-UHFFFAOYSA-N 0.000 description 1
PBUQZKXKYSAJDO-UHFFFAOYSA-M 2-[(2-methylpropan-2-yl)oxycarbonyl]benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=CC=C1C([O-])=O PBUQZKXKYSAJDO-UHFFFAOYSA-M 0.000 description 1
DZTJGKYXROFXBH-UHFFFAOYSA-N 2-[bis(sulfanyl)amino]acetic acid Chemical compound OC(=O)CN(S)S DZTJGKYXROFXBH-UHFFFAOYSA-N 0.000 description 1
UBXUDSPYIGPGGP-UHFFFAOYSA-N 2-azaniumyl-2-phenylbutanoate Chemical compound CCC(N)(C(O)=O)C1=CC=CC=C1 UBXUDSPYIGPGGP-UHFFFAOYSA-N 0.000 description 1
FKJSFKCZZIXQIP-UHFFFAOYSA-N 2-bromo-1-(4-bromophenyl)ethanone Chemical compound BrCC(=O)C1=CC=C(Br)C=C1 FKJSFKCZZIXQIP-UHFFFAOYSA-N 0.000 description 1
DIWXZZIWZCXNAM-UHFFFAOYSA-N 2-decoxy-2-oxoacetic acid Chemical compound CCCCCCCCCCOC(=O)C(O)=O DIWXZZIWZCXNAM-UHFFFAOYSA-N 0.000 description 1
APOYTRAZFJURPB-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)-n-(trifluoro-$l^{4}-sulfanyl)ethanamine Chemical compound COCCN(S(F)(F)F)CCOC APOYTRAZFJURPB-UHFFFAOYSA-N 0.000 description 1
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
KUZXQXCWRNFIHK-UHFFFAOYSA-N 3,3-diethyldodecane Chemical compound CCCCCCCCCC(CC)(CC)CC KUZXQXCWRNFIHK-UHFFFAOYSA-N 0.000 description 1
GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 1
PLXTXTKDRVJGNJ-UHFFFAOYSA-N 3-chloro-2-phenylpropanoic acid Chemical compound OC(=O)C(CCl)C1=CC=CC=C1 PLXTXTKDRVJGNJ-UHFFFAOYSA-N 0.000 description 1
FWFQXJMASKTLQD-UHFFFAOYSA-N 3-decoxyaniline Chemical compound CCCCCCCCCCOC1=CC=CC(N)=C1 FWFQXJMASKTLQD-UHFFFAOYSA-N 0.000 description 1
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
XMIIGOLPHOKFCH-UHFFFAOYSA-M 3-phenylpropionate Chemical compound [O-]C(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-M 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
XWNSFEAWWGGSKJ-UHFFFAOYSA-N 4-acetyl-4-methylheptanedinitrile Chemical compound N#CCCC(C)(C(=O)C)CCC#N XWNSFEAWWGGSKJ-UHFFFAOYSA-N 0.000 description 1
NYPIRLYMDJMKGW-VPCXQMTMSA-N 4-amino-1-[(2r,3r,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]pyrimidin-2-one Chemical compound C[C@@]1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N=C(N)C=C1 NYPIRLYMDJMKGW-VPCXQMTMSA-N 0.000 description 1
DRNGLYHKYPNTEA-UHFFFAOYSA-N 4-azaniumylcyclohexane-1-carboxylate Chemical compound NC1CCC(C(O)=O)CC1 DRNGLYHKYPNTEA-UHFFFAOYSA-N 0.000 description 1
SCRBSGZBTHKAHU-UHFFFAOYSA-N 4-bromoisoquinoline Chemical compound C1=CC=C2C(Br)=CN=CC2=C1 SCRBSGZBTHKAHU-UHFFFAOYSA-N 0.000 description 1
MUXGHJRHNFYSBX-UHFFFAOYSA-N 4-o-benzyl 1-o-methyl butanedioate Chemical compound COC(=O)CCC(=O)OCC1=CC=CC=C1 MUXGHJRHNFYSBX-UHFFFAOYSA-N 0.000 description 1
GYCPLYCTMDTEPU-UHFFFAOYSA-N 5-bromopyrimidine Chemical compound BrC1=CN=CN=C1 GYCPLYCTMDTEPU-UHFFFAOYSA-N 0.000 description 1
WTDWVLJJJOTABN-UHFFFAOYSA-N 5-cyclopropyl-2-(4-fluorophenyl)-6-[(2-hydroxyethyl)(methylsulfonyl)amino]-n-methyl-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC(N(CCO)S(C)(=O)=O)=C1C1CC1 WTDWVLJJJOTABN-UHFFFAOYSA-N 0.000 description 1
MZFPAWGWFDGCHP-UHFFFAOYSA-N 5-diphenylphosphanylpentyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 MZFPAWGWFDGCHP-UHFFFAOYSA-N 0.000 description 1
LTUZPODERZUPRD-UHFFFAOYSA-N 6-chloro-2-(1h-indol-3-yl)-4-phenylquinoline Chemical compound C12=CC(Cl)=CC=C2N=C(C=2C3=CC=CC=C3NC=2)C=C1C1=CC=CC=C1 LTUZPODERZUPRD-UHFFFAOYSA-N 0.000 description 1
SNZSSCZJMVIOCR-UHFFFAOYSA-N 7-azabicyclo[2.2.1]heptane Chemical compound C1CC2CCC1N2 SNZSSCZJMVIOCR-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
108091005508 Acid proteases Proteins 0.000 description 1
108010088751 Albumins Proteins 0.000 description 1
102000009027 Albumins Human genes 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
CKLJMWTZIZZHCS-UHFFFAOYSA-N Aspartic acid Chemical compound OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
YNAFGEKUUDLALM-UHFFFAOYSA-N C(=C)C=1C(=NC=CC1)C(=O)OCCCCCCCCCC Chemical compound C(=C)C=1C(=NC=CC1)C(=O)OCCCCCCCCCC YNAFGEKUUDLALM-UHFFFAOYSA-N 0.000 description 1
BMBNQMRZWXLHDP-SNVBAGLBSA-N C(C)(C)(C)OC([C@@H](C1=CC=CC=C1)NC(=O)N(S)S)=O Chemical compound C(C)(C)(C)OC([C@@H](C1=CC=CC=C1)NC(=O)N(S)S)=O BMBNQMRZWXLHDP-SNVBAGLBSA-N 0.000 description 1
KGKROHBZAJXQJJ-UHFFFAOYSA-N C(C)C=1C(=NC=CC1)C(=O)OCCCCCCCCCC Chemical compound C(C)C=1C(=NC=CC1)C(=O)OCCCCCCCCCC KGKROHBZAJXQJJ-UHFFFAOYSA-N 0.000 description 1
QPSVODLXFLMFDV-UHFFFAOYSA-N C(C1=CC=CC=C1)OC(C(OS(=O)(=O)C=1NC2=CC=CC=C2C1)C1=CC=CC=C1)=O Chemical compound C(C1=CC=CC=C1)OC(C(OS(=O)(=O)C=1NC2=CC=CC=C2C1)C1=CC=CC=C1)=O QPSVODLXFLMFDV-UHFFFAOYSA-N 0.000 description 1
DBXWOOKZRAIEKO-UHFFFAOYSA-N C(CC)O.[C-]#N Chemical compound C(CC)O.[C-]#N DBXWOOKZRAIEKO-UHFFFAOYSA-N 0.000 description 1
SEUKDUSQEJEYFT-UHFFFAOYSA-N C(CCCCCCCCC)(=O)OCCCCCCCCCC(N)N Chemical compound C(CCCCCCCCC)(=O)OCCCCCCCCCC(N)N SEUKDUSQEJEYFT-UHFFFAOYSA-N 0.000 description 1
OVMMDDSBHWCVSO-UHFFFAOYSA-N C(CCCCCCCCC)OC(=O)C=1C=NNC1CC Chemical compound C(CCCCCCCCC)OC(=O)C=1C=NNC1CC OVMMDDSBHWCVSO-UHFFFAOYSA-N 0.000 description 1
RANPQUOMPLOJHM-WVSUBDOOSA-N C(CCCCCCCCC)[C@@]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C=NC=2C(N)=NC=NC12 Chemical compound C(CCCCCCCCC)[C@@]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C=NC=2C(N)=NC=NC12 RANPQUOMPLOJHM-WVSUBDOOSA-N 0.000 description 1
QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 1
FMLSQIRWWXTHIQ-UHFFFAOYSA-L CCCCCCCCCCO[Sb](O)(Cl)=O Chemical compound CCCCCCCCCCO[Sb](O)(Cl)=O FMLSQIRWWXTHIQ-UHFFFAOYSA-L 0.000 description 1
HSPUWESBTWEFLQ-UHFFFAOYSA-N CCCC[Sn](CCCC)C=C Chemical compound CCCC[Sn](CCCC)C=C HSPUWESBTWEFLQ-UHFFFAOYSA-N 0.000 description 1
ZZGNBZDBLLDGOC-UHFFFAOYSA-N CN(CCN(C)C)C.NN Chemical compound CN(CCN(C)C)C.NN ZZGNBZDBLLDGOC-UHFFFAOYSA-N 0.000 description 1
KYEYJABQWFNMMG-UHFFFAOYSA-N CNN(C(N(NC)C)=O)C Chemical compound CNN(C(N(NC)C)=O)C KYEYJABQWFNMMG-UHFFFAOYSA-N 0.000 description 1
PANSTIDPOANYLJ-YFKPBYRVSA-N COC(=O)NC[C@@H](C(=O)O)CC Chemical compound COC(=O)NC[C@@H](C(=O)O)CC PANSTIDPOANYLJ-YFKPBYRVSA-N 0.000 description 1
QBBXORUQIMGZLA-UHFFFAOYSA-L CO[Sb](O)(Cl)=O Chemical compound CO[Sb](O)(Cl)=O QBBXORUQIMGZLA-UHFFFAOYSA-L 0.000 description 1
101100256918 Caenorhabditis elegans sid-2 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
229940123169 Caspase inhibitor Drugs 0.000 description 1
108090000994 Catalytic RNA Proteins 0.000 description 1
102000053642 Catalytic RNA Human genes 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
LYXCNVNNYGZUKD-QFWZMSBNSA-N Cl.C(C)(C)(C)OC([C@@H](C(C)S)N)=O Chemical compound Cl.C(C)(C)(C)OC([C@@H](C(C)S)N)=O LYXCNVNNYGZUKD-QFWZMSBNSA-N 0.000 description 1
ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 description 1
241000222239 Colletotrichum truncatum Species 0.000 description 1
229940122806 Cyclophilin inhibitor Drugs 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
ONIBWKKTOPOVIA-SCSAIBSYSA-N D-Proline Chemical compound OC(=O)[C@H]1CCCN1 ONIBWKKTOPOVIA-SCSAIBSYSA-N 0.000 description 1
229930182820 D-proline Natural products 0.000 description 1
101710118188 DNA-binding protein HU-alpha Proteins 0.000 description 1
PGIBJVOPLXHHGS-UHFFFAOYSA-N Di-n-decyl phthalate Chemical compound CCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCC PGIBJVOPLXHHGS-UHFFFAOYSA-N 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
101100136092 Drosophila melanogaster peng gene Proteins 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
241000792859 Enema Species 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
208000001613 Gambling Diseases 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
108010068370 Glutens Proteins 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
241000282412 Homo Species 0.000 description 1
241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
HAEJPQIATWHALX-KQYNXXCUSA-N ITP Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N1C(N=CNC2=O)=C2N=C1 HAEJPQIATWHALX-KQYNXXCUSA-N 0.000 description 1
108010005716 Interferon beta-1a Proteins 0.000 description 1
102000000589 Interleukin-1 Human genes 0.000 description 1
108010002352 Interleukin-1 Proteins 0.000 description 1
XIYZMOFCMDIBKI-UHFFFAOYSA-N Isolin Natural products CCC1C(OC(=O)C)C(C)C(C)(O)C(=O)OCC2=CCN3CCC(OC1=O)C23 XIYZMOFCMDIBKI-UHFFFAOYSA-N 0.000 description 1
102220517096 Jerky protein homolog-like_H49N_mutation Human genes 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
239000004395 L-leucine Substances 0.000 description 1
235000019454 L-leucine Nutrition 0.000 description 1
KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
102100020870 La-related protein 6 Human genes 0.000 description 1
108050008265 La-related protein 6 Proteins 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
108010000817 Leuprolide Proteins 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
108060001084 Luciferase Proteins 0.000 description 1
239000005089 Luciferase Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 1
NMMIHXMBOZYNET-UHFFFAOYSA-N Methyl picolinate Chemical compound COC(=O)C1=CC=CC=N1 NMMIHXMBOZYNET-UHFFFAOYSA-N 0.000 description 1
229920001410 Microfiber Polymers 0.000 description 1
RTGDFNSFWBGLEC-UHFFFAOYSA-N Mycophenolate mofetil Chemical compound COC1=C(C)C=2COC(=O)C=2C(O)=C1CC=C(C)CCC(=O)OCCN1CCOCC1 RTGDFNSFWBGLEC-UHFFFAOYSA-N 0.000 description 1
BCCOYLBBQKYHBH-UHFFFAOYSA-N N(C(=N)N)C=1C(=NC=CC1)NC(=N)N.NN Chemical compound N(C(=N)N)C=1C(=NC=CC1)NC(=N)N.NN BCCOYLBBQKYHBH-UHFFFAOYSA-N 0.000 description 1
BRMWTNUJHUMWMS-LURJTMIESA-N N(tele)-methyl-L-histidine Chemical compound CN1C=NC(C[C@H](N)C(O)=O)=C1 BRMWTNUJHUMWMS-LURJTMIESA-N 0.000 description 1
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
101710144128 Non-structural protein 2 Proteins 0.000 description 1
101710188663 Non-structural protein 5a Proteins 0.000 description 1
101710199667 Nuclear export protein Proteins 0.000 description 1
102000008021 Nucleoside-Triphosphatase Human genes 0.000 description 1
108010075285 Nucleoside-Triphosphatase Proteins 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
229910002666 PdCl2 Inorganic materials 0.000 description 1
229920002230 Pectic acid Polymers 0.000 description 1
102000035195 Peptidases Human genes 0.000 description 1
108091005804 Peptidases Proteins 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
241000276498 Pollachius virens Species 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920000331 Polyhydroxybutyrate Polymers 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000004153 Potassium bromate Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
239000004365 Protease Substances 0.000 description 1
229940124158 Protease/peptidase inhibitor Drugs 0.000 description 1
229940096437 Protein S Drugs 0.000 description 1
102000029301 Protein S Human genes 0.000 description 1
108010066124 Protein S Proteins 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
108090000944 RNA Helicases Proteins 0.000 description 1
102000004409 RNA Helicases Human genes 0.000 description 1
101710118046 RNA-directed RNA polymerase Proteins 0.000 description 1
108010012770 Rebetron Proteins 0.000 description 1
IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
UAFGCZTTXXUTHF-UHFFFAOYSA-N SC(C(C(=O)O)NCCCCCCCCCC)C Chemical compound SC(C(C(=O)O)NCCCCCCCCCC)C UAFGCZTTXXUTHF-UHFFFAOYSA-N 0.000 description 1
108091006629 SLC13A2 Proteins 0.000 description 1
XOBANOSLKMFMHP-UHFFFAOYSA-N SN(CCCCCCCCCC)S Chemical compound SN(CCCCCCCCCC)S XOBANOSLKMFMHP-UHFFFAOYSA-N 0.000 description 1
TXWCDLTYYSSRCN-SSDOTTSWSA-N SNC(N[C@@H](C(=O)O)C1=CC=CC=C1)=O Chemical compound SNC(N[C@@H](C(=O)O)C1=CC=CC=C1)=O TXWCDLTYYSSRCN-SSDOTTSWSA-N 0.000 description 1
PSMZBKVMDPSDKH-UHFFFAOYSA-N SSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSS Chemical compound SSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSS PSMZBKVMDPSDKH-UHFFFAOYSA-N 0.000 description 1
241000207929 Scutellaria Species 0.000 description 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
101710102218 Serine protease inhibitor Proteins 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
101710172711 Structural protein Proteins 0.000 description 1
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
241001231783 Teira Species 0.000 description 1
PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
108010046075 Thymosin Proteins 0.000 description 1
102000007501 Thymosin Human genes 0.000 description 1
102000008235 Toll-Like Receptor 9 Human genes 0.000 description 1
108010060818 Toll-Like Receptor 9 Proteins 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
241000009298 Trigla lyra Species 0.000 description 1
101000956368 Trittame loki CRISP/Allergen/PR-1 Proteins 0.000 description 1
229940122429 Tubulin inhibitor Drugs 0.000 description 1
108091023045 Untranslated Region Proteins 0.000 description 1
208000036142 Viral infection Diseases 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
TVRCRTJYMVTEFS-ICGCPXGVSA-N [(2r,3r,4r,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)-4-methyloxolan-3-yl] (2s)-2-amino-3-methylbutanoate Chemical compound C[C@@]1(O)[C@H](OC(=O)[C@@H](N)C(C)C)[C@@H](CO)O[C@H]1N1C(=O)N=C(N)C=C1 TVRCRTJYMVTEFS-ICGCPXGVSA-N 0.000 description 1
ROAVTVXTYFSQEA-UHFFFAOYSA-N [2-(4-bromophenyl)-2-oxoethyl]azanium;chloride Chemical compound [Cl-].[NH3+]CC(=O)C1=CC=C(Br)C=C1 ROAVTVXTYFSQEA-UHFFFAOYSA-N 0.000 description 1
YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
PLXQGEWNITUHNB-UHFFFAOYSA-N [La]=O Chemical compound [La]=O PLXQGEWNITUHNB-UHFFFAOYSA-N 0.000 description 1
RLYJYLOIDKPGGZ-UHFFFAOYSA-N [Ru+].C1=CC=CCCCC1 Chemical compound [Ru+].C1=CC=CCCCC1 RLYJYLOIDKPGGZ-UHFFFAOYSA-N 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
239000003655 absorption accelerator Substances 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
CDSUEGXTPYWXAB-UHFFFAOYSA-N acetic acid ethyl acetate Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.CCOC(C)=O CDSUEGXTPYWXAB-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
235000004279 alanine Nutrition 0.000 description 1
108010080374 albuferon Proteins 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
150000001345 alkine derivatives Chemical class 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
BAZMYXGARXYAEQ-UHFFFAOYSA-N alpha-ethyl valeric acid Chemical compound CCCC(CC)C(O)=O BAZMYXGARXYAEQ-UHFFFAOYSA-N 0.000 description 1
ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000003862 amino acid derivatives Chemical class 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000001093 anti-cancer Effects 0.000 description 1
230000002300 anti-fibrosis Effects 0.000 description 1
230000000692 anti-sense effect Effects 0.000 description 1
230000002421 anti-septic effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
239000008122 artificial sweetener Substances 0.000 description 1
235000021311 artificial sweeteners Nutrition 0.000 description 1
125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 1
150000001502 aryl halides Chemical class 0.000 description 1
125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-L aspartate group Chemical class N[C@@H](CC(=O)[O-])C(=O)[O-] CKLJMWTZIZZHCS-REOHCLBHSA-L 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
229950001429 batabulin Drugs 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
RLMHWGDKMJIEHH-QRPNPIFTSA-N benzyl (2s)-2-aminopropanoate;hydrochloride Chemical compound Cl.C[C@H](N)C(=O)OCC1=CC=CC=C1 RLMHWGDKMJIEHH-QRPNPIFTSA-N 0.000 description 1
JFKWZVQEMSKSBU-AWEZNQCLSA-N benzyl (2s)-2-hydroxy-2-phenylacetate Chemical compound O=C([C@@H](O)C=1C=CC=CC=1)OCC1=CC=CC=C1 JFKWZVQEMSKSBU-AWEZNQCLSA-N 0.000 description 1
YMXYKUNTQVTWSH-ZTOMLWHTSA-N benzyl (2s,3r)-4-hydroxy-3-methyl-2-[(9-phenylfluoren-9-yl)amino]butanoate Chemical compound N([C@@H]([C@H](CO)C)C(=O)OCC=1C=CC=CC=1)C1(C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 YMXYKUNTQVTWSH-ZTOMLWHTSA-N 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
210000000941 bile Anatomy 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
229920002988 biodegradable polymer Polymers 0.000 description 1
239000004621 biodegradable polymer Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
229910052797 bismuth Inorganic materials 0.000 description 1
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
238000005422 blasting Methods 0.000 description 1
229920001400 block copolymer Polymers 0.000 description 1
230000037396 body weight Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000001273 butane Substances 0.000 description 1
150000004648 butanoic acid derivatives Chemical class 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
108010022387 calmodulin acceptor protein 60 Proteins 0.000 description 1
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
POIUWJQBRNEFGX-XAMSXPGMSA-N cathelicidin Chemical compound C([C@@H](C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(O)=O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CC(C)C)C1=CC=CC=C1 POIUWJQBRNEFGX-XAMSXPGMSA-N 0.000 description 1
238000005341 cation exchange Methods 0.000 description 1
210000000170 cell membrane Anatomy 0.000 description 1
229940107810 cellcept Drugs 0.000 description 1
229910000420 cerium oxide Inorganic materials 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
229940106681 chloroacetic acid Drugs 0.000 description 1
ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
PJZPDFUUXKKDNB-KNINVFKUSA-N ciluprevir Chemical compound N([C@@H]1C(=O)N2[C@H](C(N[C@@]3(C[C@H]3\C=C/CCCCC1)C(O)=O)=O)C[C@H](C2)OC=1C2=CC=C(C=C2N=C(C=1)C=1N=C(NC(C)C)SC=1)OC)C(=O)OC1CCCC1 PJZPDFUUXKKDNB-KNINVFKUSA-N 0.000 description 1
208000019425 cirrhosis of liver Diseases 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
235000017471 coenzyme Q10 Nutrition 0.000 description 1
108010052008 colla corii asini Proteins 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000002648 combination therapy Methods 0.000 description 1
230000006957 competitive inhibition Effects 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
238000012937 correction Methods 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical class C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
XZSPDZZPOWEABC-UHFFFAOYSA-N cyanide Chemical compound N#[C-].N#[C-] XZSPDZZPOWEABC-UHFFFAOYSA-N 0.000 description 1
125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 description 1
125000005144 cycloalkylsulfonyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
239000000134 cyclophilin inhibitor Substances 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
229930182912 cyclosporin Natural products 0.000 description 1
230000006378 damage Effects 0.000 description 1
XAKXZZPEUKNHMA-UHFFFAOYSA-N decyl decanoate Chemical compound CCCCCCCCCCOC(=O)CCCCCCCCC XAKXZZPEUKNHMA-UHFFFAOYSA-N 0.000 description 1
125000006612 decyloxy group Chemical group 0.000 description 1
230000007123 defense Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
210000004207 dermis Anatomy 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
UCVPKAZCQPRWAY-UHFFFAOYSA-N dibenzyl benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC=2C=CC=CC=2)C=1C(=O)OCC1=CC=CC=C1 UCVPKAZCQPRWAY-UHFFFAOYSA-N 0.000 description 1
LWDBCTRJOMGAPB-UHFFFAOYSA-N dichlorocarbamic acid Chemical compound OC(=O)N(Cl)Cl LWDBCTRJOMGAPB-UHFFFAOYSA-N 0.000 description 1
LCSNDSFWVKMJCT-UHFFFAOYSA-N dicyclohexyl-(2-phenylphenyl)phosphane Chemical group C1CCCCC1P(C=1C(=CC=CC=1)C=1C=CC=CC=1)C1CCCCC1 LCSNDSFWVKMJCT-UHFFFAOYSA-N 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
229930004069 diterpene Natural products 0.000 description 1
238000001035 drying Methods 0.000 description 1
229950000234 emricasan Drugs 0.000 description 1
239000007920 enema Substances 0.000 description 1
229940079360 enema for constipation Drugs 0.000 description 1
210000002615 epidermis Anatomy 0.000 description 1
230000001973 epigenetic effect Effects 0.000 description 1
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
BGCNBOFPABQGNG-UHFFFAOYSA-N ethyl 2-(dimethylamino)acetate Chemical compound CCOC(=O)CN(C)C BGCNBOFPABQGNG-UHFFFAOYSA-N 0.000 description 1
QVLJLWHOILVHJJ-UHFFFAOYSA-N ethyl 2-pyridin-4-ylacetate Chemical compound CCOC(=O)CC1=CC=NC=C1 QVLJLWHOILVHJJ-UHFFFAOYSA-N 0.000 description 1
ATBLMLKOVBKADA-UHFFFAOYSA-N ethyl acetate;hexane Chemical class CCCCCC.CCCCCC.CCOC(C)=O ATBLMLKOVBKADA-UHFFFAOYSA-N 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
230000029142 excretion Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
210000000887 face Anatomy 0.000 description 1
LLGDPTDZOVKFDU-XUHJSTDZSA-N faldaprevir Chemical compound N([C@H](C(=O)N1[C@@H](C[C@H](C1)OC=1C2=CC=C(C(=C2N=C(C=1)C=1N=C(NC(=O)C(C)C)SC=1)Br)OC)C(=O)N[C@]1([C@@H](C1)C=C)C(O)=O)C(C)(C)C)C(=O)OC1CCCC1 LLGDPTDZOVKFDU-XUHJSTDZSA-N 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
SLVAPEZTBDBAPI-GDLZYMKVSA-N filibuvir Chemical compound CCC1=NC(CC)=CC(CC[C@]2(OC(=O)C(CC3=NN4C(C)=CC(C)=NC4=N3)=C(O)C2)C2CCCC2)=C1 SLVAPEZTBDBAPI-GDLZYMKVSA-N 0.000 description 1
239000010419 fine particle Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000005454 flavour additive Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000003292 glue Substances 0.000 description 1
229930195712 glutamate Natural products 0.000 description 1
235000021312 gluten Nutrition 0.000 description 1
150000002332 glycine derivatives Chemical class 0.000 description 1
229930182470 glycoside Natural products 0.000 description 1
150000002338 glycosides Chemical class 0.000 description 1
230000005484 gravity Effects 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
229910052736 halogen Chemical group 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
206010073071 hepatocellular carcinoma Diseases 0.000 description 1
231100000844 hepatocellular carcinoma Toxicity 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
125000006588 heterocycloalkylene group Chemical group 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
102000011749 human hepatitis C immune globulin Human genes 0.000 description 1
108010062138 human hepatitis C immune globulin Proteins 0.000 description 1
244000052637 human pathogen Species 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
239000000017 hydrogel Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
125000005182 hydroxyalkylcarbonyl group Chemical group 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
229940090438 infergen Drugs 0.000 description 1
238000001802 infusion Methods 0.000 description 1
108010010648 interferon alfacon-1 Proteins 0.000 description 1
108010042414 interferon gamma-1b Proteins 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007919 intrasynovial administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
230000000622 irritating effect Effects 0.000 description 1
230000007794 irritation Effects 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 description 1
WCRKBMABEPCYII-UHFFFAOYSA-N isoquinolin-7-ol Chemical compound C1=CN=CC2=CC(O)=CC=C21 WCRKBMABEPCYII-UHFFFAOYSA-N 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
238000002372 labelling Methods 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
229960003136 leucine Drugs 0.000 description 1
GFIJNRVAKGFPGQ-LIJARHBVSA-N leuprolide Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 GFIJNRVAKGFPGQ-LIJARHBVSA-N 0.000 description 1
229960004338 leuprorelin Drugs 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
208000019423 liver disease Diseases 0.000 description 1
230000007762 localization of cell Effects 0.000 description 1
239000006210 lotion Substances 0.000 description 1
210000004698 lymphocyte Anatomy 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
239000001525 mentha piperita l. herb oil Substances 0.000 description 1
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
229950003168 merimepodib Drugs 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 1
UHNSRFWQBVXBSK-UHFFFAOYSA-N methanol;2,2,2-trifluoroacetic acid Chemical compound OC.OC(=O)C(F)(F)F UHNSRFWQBVXBSK-UHFFFAOYSA-N 0.000 description 1
WEDZBNHWDBCBEF-UHFFFAOYSA-N methyl 3-(trifluoromethylsulfonyloxy)pyridine-2-carboxylate Chemical compound COC(=O)C1=NC=CC=C1OS(=O)(=O)C(F)(F)F WEDZBNHWDBCBEF-UHFFFAOYSA-N 0.000 description 1
WFNCZUIGZZVNKH-UHFFFAOYSA-N methyl 3-ethylpyridine-2-carboxylate Chemical compound CCC1=CC=CN=C1C(=O)OC WFNCZUIGZZVNKH-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 description 1
239000003658 microfiber Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
150000004712 monophosphates Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
210000000214 mouth Anatomy 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 description 1
RIVIDPPYRINTTH-UHFFFAOYSA-N n-ethylpropan-2-amine Chemical compound CCNC(C)C RIVIDPPYRINTTH-UHFFFAOYSA-N 0.000 description 1
OHDXDNUPVVYWOV-UHFFFAOYSA-N n-methyl-1-(2-naphthalen-1-ylsulfanylphenyl)methanamine Chemical compound CNCC1=CC=CC=C1SC1=CC=CC2=CC=CC=C12 OHDXDNUPVVYWOV-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
210000004897 n-terminal region Anatomy 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
239000007923 nasal drop Substances 0.000 description 1
229940100662 nasal drops Drugs 0.000 description 1
229940052404 nasal powder Drugs 0.000 description 1
239000002014 nasya oil Substances 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
229960002715 nicotine Drugs 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
RPJPZDVUUKWPGT-FOIHOXPVSA-N nim811 Chemical compound CC[C@H](C)[C@@H]1N(C)C(=O)CN(C)C(=O)[C@H](CC)NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC1=O RPJPZDVUUKWPGT-FOIHOXPVSA-N 0.000 description 1
DVNDIRCCXAOUIZ-UHFFFAOYSA-N nonoxycarbonyl nonyl carbonate Chemical compound CCCCCCCCCOC(=O)OC(=O)OCCCCCCCCC DVNDIRCCXAOUIZ-UHFFFAOYSA-N 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
125000003729 nucleotide group Chemical group 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
IUCHKMAZAWJNBJ-RCYXVVTDSA-N oleanolic acid 3-O-beta-D-glucosiduronic acid Chemical compound O([C@H]1CC[C@]2(C)[C@H]3CC=C4[C@@]([C@@]3(CC[C@H]2C1(C)C)C)(C)CC[C@]1(CCC(C[C@H]14)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O IUCHKMAZAWJNBJ-RCYXVVTDSA-N 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Chemical group CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000008506 pathogenesis Effects 0.000 description 1
229940002988 pegasys Drugs 0.000 description 1
229940106366 pegintron Drugs 0.000 description 1
JXBYFMOVLAYYCN-UHFFFAOYSA-N pentaoxan-6-ol Chemical compound O1OOOOC1O JXBYFMOVLAYYCN-UHFFFAOYSA-N 0.000 description 1
235000019477 peppermint oil Nutrition 0.000 description 1
239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
229940075930 picrate Drugs 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
LEGMHPGYPXPXKB-UHFFFAOYSA-N piperidin-2-ol Chemical compound OC1CCCCN1 LEGMHPGYPXPXKB-UHFFFAOYSA-N 0.000 description 1
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
239000005015 poly(hydroxybutyrate) Substances 0.000 description 1
229920000747 poly(lactic acid) Polymers 0.000 description 1
229920001610 polycaprolactone Polymers 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
229920002721 polycyanoacrylate Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
230000003234 polygenic effect Effects 0.000 description 1
239000004626 polylactic acid Substances 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
150000004032 porphyrins Chemical class 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
229910000343 potassium bisulfate Inorganic materials 0.000 description 1
229940094037 potassium bromate Drugs 0.000 description 1
235000019396 potassium bromate Nutrition 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical class [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
TTZHDVOVKQGIBA-IAAJYNJHSA-N propan-2-yl (2s)-2-[[[(2r,3r,4r,5r)-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyloxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate Chemical compound N1([C@@H]2O[C@@H]([C@H]([C@]2(F)C)O)COP(=O)(N[C@@H](C)C(=O)OC(C)C)OC=2C=CC=CC=2)C=CC(=O)NC1=O TTZHDVOVKQGIBA-IAAJYNJHSA-N 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
239000011253 protective coating Substances 0.000 description 1
230000017854 proteolysis Effects 0.000 description 1
239000013014 purified material Substances 0.000 description 1
125000006085 pyrrolopyridyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
239000001397 quillaja saponaria molina bark Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
230000010076 replication Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
229960000329 ribavirin Drugs 0.000 description 1
HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 1
108091092562 ribozyme Proteins 0.000 description 1
108700022109 ropocamptide Proteins 0.000 description 1
BIXNGBXQRRXPLM-UHFFFAOYSA-K ruthenium(3+);trichloride;hydrate Chemical compound O.Cl[Ru](Cl)Cl BIXNGBXQRRXPLM-UHFFFAOYSA-K 0.000 description 1
239000004576 sand Substances 0.000 description 1
229930182490 saponin Natural products 0.000 description 1
150000007949 saponins Chemical class 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
238000005201 scrubbing Methods 0.000 description 1
239000000565 sealant Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
DEKOYVOWOVJMPM-RLHIPHHXSA-N setrobuvir Chemical compound N1([C@H]2[C@@H]3CC[C@@H](C3)[C@H]2C(O)=C(C1=O)C=1NC2=CC=C(C=C2S(=O)(=O)N=1)NS(=O)(=O)C)CC1=CC=C(F)C=C1 DEKOYVOWOVJMPM-RLHIPHHXSA-N 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
239000004208 shellac Substances 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000020374 simple syrup Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000011684 sodium molybdate Substances 0.000 description 1
235000015393 sodium molybdate Nutrition 0.000 description 1
TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
SSERCMQZZYTNBY-UHFFFAOYSA-M sodium;3-[(4-hydroxycyclohexyl)-(4-methylcyclohexanecarbonyl)amino]-5-phenylthiophene-2-carboxylate Chemical compound [Na+].C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1C=CC=CC=1)C([O-])=O)C1CCC(O)CC1 SSERCMQZZYTNBY-UHFFFAOYSA-M 0.000 description 1
239000008279 sol Substances 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
125000006850 spacer group Chemical group 0.000 description 1
241000894007 species Species 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
229910052596 spinel Inorganic materials 0.000 description 1
239000011029 spinel Substances 0.000 description 1
HPRAYQNGLXYUQM-UHFFFAOYSA-N spiro[4.5]decane-1,4,8-trione Chemical compound O=C1CCC(=O)C11CCC(=O)CC1 HPRAYQNGLXYUQM-UHFFFAOYSA-N 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000004808 supercritical fluid chromatography Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000001648 tannin Substances 0.000 description 1
235000018553 tannin Nutrition 0.000 description 1
229920001864 tannin Polymers 0.000 description 1
229910052715 tantalum Inorganic materials 0.000 description 1
GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
229960002935 telaprevir Drugs 0.000 description 1
108010017101 telaprevir Proteins 0.000 description 1
125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical group [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
125000003554 tetrahydropyrrolyl group Chemical group 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000011285 therapeutic regimen Methods 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
229940062627 tribasic potassium phosphate Drugs 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
229940066528 trichloroacetate Drugs 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
RGUFCXSDKOITOF-UHFFFAOYSA-N tridecylstannane Chemical compound C(CCCCCCCCCCCC)[SnH3] RGUFCXSDKOITOF-UHFFFAOYSA-N 0.000 description 1
229930191535 trisporin Natural products 0.000 description 1
150000003648 triterpenes Chemical class 0.000 description 1
238000001665 trituration Methods 0.000 description 1
229940035936 ubiquinone Drugs 0.000 description 1
229940120293 vaginal suppository Drugs 0.000 description 1
239000006216 vaginal suppository Substances 0.000 description 1
238000010200 validation analysis Methods 0.000 description 1
238000012795 verification Methods 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
210000002845 virion Anatomy 0.000 description 1
239000008215 water for injection Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Virology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Epidemiology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Dermatology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Plural Heterocyclic Compounds (AREA)
Medicinal Preparation (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Peptides Or Proteins (AREA)

TW099109167A 2009-04-09 2010-03-26 Hepatitis C virus inhibitors TW201038559A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US16798909P	2009-04-09	2009-04-09

Publications (1)

Publication Number	Publication Date
TW201038559A true TW201038559A (en)	2010-11-01

Family

ID=42244128

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW099109167A TW201038559A (en)	2009-04-09	2010-03-26	Hepatitis C virus inhibitors

Country Status (22)

Country	Link
US (1)	US8143301B2 (es)
EP (1)	EP2417126B1 (es)
JP (1)	JP5558556B2 (es)
KR (1)	KR20120133366A (es)
CN (1)	CN102803249B (es)
AR (1)	AR076274A1 (es)
AU (1)	AU2010234608B2 (es)
BR (1)	BRPI1010506A2 (es)
CA (1)	CA2757963A1 (es)
CL (1)	CL2011002524A1 (es)
CO (1)	CO6440581A2 (es)
EA (1)	EA018793B1 (es)
ES (1)	ES2502667T3 (es)
IL (1)	IL215095A0 (es)
MX (1)	MX2011010478A (es)
MY (1)	MY152971A (es)
NZ (1)	NZ595186A (es)
PE (1)	PE20120533A1 (es)
SG (1)	SG174582A1 (es)
TW (1)	TW201038559A (es)
WO (1)	WO2010117977A1 (es)
ZA (1)	ZA201107095B (es)

Families Citing this family (79)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2505540C2 (ru)	2008-12-23	2014-01-27	Эббви Инк.	Антивирусные соединения
CA2740195A1 (en)	2008-12-23	2010-07-01	Abbott Laboratories	Anti-viral compounds
US8314135B2 (en) *	2009-02-09	2012-11-20	Enanta Pharmaceuticals, Inc.	Linked dibenzimidazole antivirals
US8188132B2 (en)	2009-02-17	2012-05-29	Enanta Pharmaceuticals, Inc.	Linked dibenzimidazole derivatives
US8242156B2 (en)	2009-02-17	2012-08-14	Enanta Pharmaceuticals, Inc.	Linked dibenzimidazole derivatives
US8394968B2 (en)	2009-02-17	2013-03-12	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
TWI438200B (zh) *	2009-02-17	2014-05-21	必治妥美雅史谷比公司	Ｃ型肝炎病毒抑制劑
US8673954B2 (en)	2009-02-27	2014-03-18	Enanta Pharmaceuticals, Inc.	Benzimidazole derivatives
US8101643B2 (en) *	2009-02-27	2012-01-24	Enanta Pharmaceuticals, Inc.	Benzimidazole derivatives
US9765087B2 (en)	2009-02-27	2017-09-19	Enanta Pharmaceuticals, Inc.	Benzimidazole derivatives
US8796466B2 (en)	2009-03-30	2014-08-05	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US8143414B2 (en)	2009-04-13	2012-03-27	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
RU2541571C2 (ru) *	2009-04-15	2015-02-20	Эббви Инк.	Противовирусные соединения
MX360800B (es)	2009-05-13	2018-11-16	Gilead Pharmasset Llc Star	Compuestos antivirales.
US8211928B2 (en)	2009-05-29	2012-07-03	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US8138215B2 (en)	2009-05-29	2012-03-20	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US8937150B2 (en)	2009-06-11	2015-01-20	Abbvie Inc.	Anti-viral compounds
AR077060A1 (es) *	2009-06-11	2011-07-27	Abbott Lab	Compuestos antivirales
US9394279B2 (en)	2009-06-11	2016-07-19	Abbvie Inc.	Anti-viral compounds
US8716454B2 (en)	2009-06-11	2014-05-06	Abbvie Inc.	Solid compositions
US8221737B2 (en) *	2009-06-16	2012-07-17	Enanta Pharmaceuticals, Inc.	Hepatitis C virus inhibitors
US8609648B2 (en)	2009-07-02	2013-12-17	Enanta Pharmaceuticals, Inc.	Hepatitis C virus inhibitors
MX2012000695A (es)	2009-07-16	2012-06-12	Vertex Pharma	Análogos de bencimidazol para el tratamiento o la prevención de infecciones por flavivirus.
CN102480971B (zh)	2009-09-04	2014-11-26	杨森制药公司	化合物
US8927709B2 (en) *	2009-09-11	2015-01-06	Enanta Pharmaceuticals, Inc.	Hepatitis C virus inhibitors
US8759332B2 (en) *	2009-09-11	2014-06-24	Enanta Pharmaceuticals, Inc.	Hepatitis C virus inhibitors
US8703938B2 (en) *	2009-09-11	2014-04-22	Enanta Pharmaceuticals, Inc.	Hepatitis C virus inhibitors
US8822700B2 (en) *	2009-09-11	2014-09-02	Enanta Pharmaceuticals, Inc.	Hepatitis C virus inhibitors
US8815928B2 (en)	2009-09-11	2014-08-26	Enanta Pharmaceuticals, Inc.	Hepatitis C virus inhibitors
EP2475256A4 (en) *	2009-09-11	2013-06-05	Enanta Pharm Inc	HEPATITIS C-VIRUS HEMMER
US20110274648A1 (en)	2009-11-11	2011-11-10	Bristol-Myers Squibb Company	Hepatitis C Virus Inhibitors
US20110269956A1 (en)	2009-11-11	2011-11-03	Bristol-Myers Squibb Company	Hepatitis C Virus Inhibitors
US20110281910A1 (en)	2009-11-12	2011-11-17	Bristol-Myers Squibb Company	Hepatitis C Virus Inhibitors
US20110137633A1 (en) *	2009-12-03	2011-06-09	Abbott Laboratories	Anti-viral compounds and methods of identifying the same
US8653070B2 (en) *	2009-12-14	2014-02-18	Enanta Pharmaceuticals, Inc.	Hepatitis C virus inhibitors
US8377980B2 (en)	2009-12-16	2013-02-19	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
CN102791687B (zh) *	2009-12-18	2015-02-11	北京凯因科技股份有限公司	C型肝炎病毒复制的新型抑制剂
US8362020B2 (en)	2009-12-30	2013-01-29	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
JP2013518060A (ja)	2010-01-25	2013-05-20	エナンタファーマシューティカルズインコーポレイテッド	Ｃ型肝炎ウイルス阻害剤
US8933110B2 (en)	2010-01-25	2015-01-13	Enanta Pharmaceuticals, Inc.	Hepatitis C virus inhibitors
US8623814B2 (en) *	2010-02-23	2014-01-07	Enanta Pharmaceuticals, Inc.	Antiviral agents
US8178531B2 (en) *	2010-02-23	2012-05-15	Enanta Pharmaceuticals, Inc.	Antiviral agents
AU2010347272A1 (en) *	2010-03-04	2012-09-20	Enanta Pharmaceuticals, Inc.	Combination pharmaceutical agents as inhibitors of HCV replication
CA2794145A1 (en)	2010-03-24	2011-09-29	Vertex Pharmaceuticals Incorporated	Analogues for the treatment or prevention of flavivirus infections
WO2011127350A1 (en)	2010-04-09	2011-10-13	Enanta Pharmaceuticals, Inc.	Hepatitis c virus inhibitors
WO2011153396A1 (en)	2010-06-04	2011-12-08	Enanta Pharmaceuticals, Inc	Hepatitis c virus inhibitors
NZ605440A (en)	2010-06-10	2014-05-30	Abbvie Bahamas Ltd	Solid compositions comprising an hcv inhibitor
EP2585447A2 (en)	2010-06-28	2013-05-01	Vertex Pharmaceuticals Incorporated	Compounds and methods for the treatment or prevention of flavivirus infections
EP2585448A1 (en)	2010-06-28	2013-05-01	Vertex Pharmaceuticals Incorporated	Compounds and methods for the treatment or prevention of flavivirus infections
EP2603080A4 (en)	2010-08-12	2014-01-22	Enanta Pharm Inc	HEPATITIS C-VIRUS HEMMER
CN103153978A (zh)	2010-08-17	2013-06-12	沃泰克斯药物股份有限公司	用于治疗或预防黄病毒科病毒感染的化合物和方法
RU2452735C1 (ru)	2010-11-30	2012-06-10	Александр Васильевич Иващенко	Замещенные азолы, противовирусный активный компонент, фармацевтическая композиция, способ получения и применения
CA2819894A1 (en) *	2010-12-16	2012-06-21	Abbvie Inc.	Anti-viral compounds
JP5918264B2 (ja)	2010-12-22	2016-05-18	アッヴィ・インコーポレイテッド	Ｃ型肝炎阻害剤およびその使用
US8552047B2 (en)	2011-02-07	2013-10-08	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US9546160B2 (en)	2011-05-12	2017-01-17	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US10201584B1 (en)	2011-05-17	2019-02-12	Abbvie Inc.	Compositions and methods for treating HCV
WO2012158861A2 (en)	2011-05-18	2012-11-22	Enanta Pharmaceuticals, Inc.	Processes for the preparation of 5-azaspiro[2.4]heptane-6-carboxylic acid and its derivatives
WO2013016499A1 (en)	2011-07-26	2013-01-31	Vertex Pharmaceuticals Incorporated	Methods for preparation of thiophene compounds
AR087345A1 (es)	2011-07-26	2014-03-19	Vertex Pharma	Metodos para la preparacion de compuestos de tiofeno
WO2013030750A1 (en)	2011-09-01	2013-03-07	Lupin Limited	Antiviral compounds
SG11201400664WA (en)	2011-09-16	2014-04-28	Gilead Pharmassett Llc	Methods for treating hcv
US9034832B2 (en)	2011-12-29	2015-05-19	Abbvie Inc.	Solid compositions
US9326973B2 (en)	2012-01-13	2016-05-03	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
NZ628515A (en)	2012-02-10	2016-06-24	Lupin Ltd	Antiviral compounds with a dibenzooxaheterocycle moiety
HK1203356A1 (en)	2012-03-22	2015-10-30	艾丽奥斯生物制药有限公司	Pharmaceutical combinations comprising a thionucleotide analog
US20140212491A1 (en)	2013-01-31	2014-07-31	Gilead Pharmasset Llc	Combination formulation of two antiviral compounds
RU2507201C1 (ru)	2013-02-07	2014-02-20	Александр Васильевич Иващенко	Алкил [(s)-1-((s)-2-{5-[4-(4-{2-[(s)-1-((s)-2-метоксикарбониламино-3-метил-бутирил)-пирролидин-2-ил]-3н-имидазол-4-ил}-бута-1,3-диинил)-фенил]-1н-имидазол-2-ил}-пирролидин-1-карбонил)-2-метил-пропил]-карбамат нафталин-1,5-дисульфонат, фармацевтическая композиция, лекарственное средство, способ лечения вирусных заболеваний
TW201526899A (zh)	2013-02-28	2015-07-16	Alios Biopharma Inc	醫藥組成物
US11484534B2 (en)	2013-03-14	2022-11-01	Abbvie Inc.	Methods for treating HCV
US9717712B2 (en)	2013-07-02	2017-08-01	Bristol-Myers Squibb Company	Combinations comprising tricyclohexadecahexaene derivatives for use in the treatment of hepatitis C virus
US20150023913A1 (en)	2013-07-02	2015-01-22	Bristol-Myers Squibb Company	Hepatitis C Virus Inhibitors
US9775831B2 (en)	2013-07-17	2017-10-03	Bristol-Myers Squibb Company	Combinations comprising biphenyl derivatives for use in the treatment of HCV
EP3038601B1 (en)	2013-08-27	2020-04-08	Gilead Pharmasset LLC	Combination formulation of two antiviral compounds
EP3089757A1 (en)	2014-01-03	2016-11-09	AbbVie Inc.	Solid antiviral dosage forms
US10617675B2 (en)	2015-08-06	2020-04-14	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
KR102497854B1 (ko)	2017-11-12	2023-02-07	대우조선해양 주식회사	함 내 연료전지 운용 시스템 및 운용 방법
JP7723119B2 (ja)	2021-05-21	2025-08-13	ギリアードサイエンシーズ，インコーポレイテッド	ジカウイルス感染症の治療のための四環系化合物
WO2022246109A1 (en)	2021-05-21	2022-11-24	Gilead Sciences, Inc.	Pentacyclic derivatives as zika virus inhibitors

Family Cites Families (81)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2153987A1 (en)	1993-01-14	1994-07-21	U. Prasad Kari	Amino acids and peptides having modified terminals
US5654451B1 (en)	1993-01-14	2000-02-22	Magainin Pharma	Amino acids and peptides having modified c-terminals and modified n-terminals
AU2003249977A1 (en)	2002-07-05	2004-01-23	Axxima Pharmaceuticals Ag	Imidazole compounds for the treatment of hepatitis c virus infections
PE20060426A1 (es) *	2004-06-02	2006-06-28	Schering Corp	DERIVADOS DE ACIDO TARTARICO COMO INHIBIDORES DE MMPs, ADAMs, TACE Y TNF-alfa
WO2006022442A1 (ja)	2004-08-24	2006-03-02	Santen Pharmaceutical Co., Ltd.	ジヒドロオロテートデヒドロゲナーゼ阻害活性を有する新規複素環アミド誘導体
US7894996B2 (en)	2005-02-28	2011-02-22	The Rockefeller University	Structure of the hepatitis C NS5A protein
US8143288B2 (en)	2005-06-06	2012-03-27	Bristol-Myers Squibb Company	Inhibitors of HCV replication
AU2006290442B2 (en)	2005-09-16	2010-07-29	Arrow Therapeutics Limited	Biphenyl derivatives and their use in treating hepatitis C
WO2007058384A1 (en)	2005-11-17	2007-05-24	Osaka University	Method of suppressing replication of hepatitis c virus, inhibitor of replication of the virus and method of screening for the same
WO2007081517A2 (en)	2005-12-21	2007-07-19	Abbott Laboratories	Anti-viral compounds
US7910595B2 (en)	2005-12-21	2011-03-22	Abbott Laboratories	Anti-viral compounds
SG133452A1 (en)	2005-12-30	2007-07-30	Novartis Ag	Peptide deformylase inhibitors for treatment of mycobacterial and other parasitic diseases
AU2007266915A1 (en)	2006-05-30	2007-12-06	Arrow Therapeutics Limited	Biphenyl derivatives and their use in treating hepatitis C
CA2672267C (en)	2006-07-27	2016-05-31	Emisphere Technologies, Inc.	Arylsulfanyl compounds and compositions for delivering active agents
US8303944B2 (en) *	2006-08-11	2012-11-06	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US7759495B2 (en)	2006-08-11	2010-07-20	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US8329159B2 (en)	2006-08-11	2012-12-11	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US7659270B2 (en)	2006-08-11	2010-02-09	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US20100158862A1 (en)	2006-08-11	2010-06-24	Bristol-Myers Squibb Company	Hepatitis C Virus Inhibitors
TW200831084A (en)	2006-11-21	2008-08-01	Genelabs Tech Inc	Anti-viral compounds
EP2094276A4 (en)	2006-12-20	2011-01-05	Abbott Lab	ANTIVIRAL COMPOUNDS
US7728027B2 (en)	2007-08-08	2010-06-01	Bristol-Myers Squibb Company	Process for synthesizing compounds useful for treating hepatitis C
US8629171B2 (en)	2007-08-08	2014-01-14	Bristol-Myers Squibb Company	Crystalline form of methyl ((1S)-1-((25)-2-(5-(4'-(2-((25)-1((2S)-2-((methoxycarbonyl)amino)-3-methylbutanoyl)-2-pyrrolidinyl)-1H-imidazol-2-yl)-1-pyrrolidinyl)carbonyl)-2-methylpropyl)carbamate dihydrochloride salt
US8093243B2 (en)	2008-02-12	2012-01-10	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
WO2009102318A1 (en)	2008-02-12	2009-08-20	Bristol-Myers Squibb Company	Hepatitis c virus inhibitors
US7704992B2 (en)	2008-02-13	2010-04-27	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
BRPI0822323A2 (pt)	2008-02-13	2015-06-16	Bristol Myers Squibb Co	Imidazolil bifenil imidazóis como inibidores do vírus da hepatite c
US8147818B2 (en)	2008-02-13	2012-04-03	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US7906655B2 (en)	2008-08-07	2011-03-15	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US8383094B2 (en)	2008-10-01	2013-02-26	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US8729077B2 (en)	2008-11-28	2014-05-20	Glaxosmithkline Llc	Anti-viral compounds, compositions, and methods of use
EP2682393A1 (en)	2008-12-03	2014-01-08	Presidio Pharmaceuticals, Inc.	Inhibitors of HCV NS5A comprising a bicyclic core.
KR20110098779A (ko)	2008-12-03	2011-09-01	프레시디오 파마슈티칼스, 인코포레이티드	Ｈｃｖｎｓ5ａ의 억제제
RU2505540C2 (ru)	2008-12-23	2014-01-27	Эббви Инк.	Антивирусные соединения
WO2010091413A1 (en)	2009-02-09	2010-08-12	Enanta Pharmaceuticals, Inc.	Linked dibenzimidazole derivatives
WO2010096462A1 (en)	2009-02-17	2010-08-26	Enanta Pharmaceuticals, Inc	Linked diimidazole derivatives
TWI438200B (zh)	2009-02-17	2014-05-21	必治妥美雅史谷比公司	Ｃ型肝炎病毒抑制劑
WO2010096777A1 (en)	2009-02-23	2010-08-26	Presidio Pharmaceuticals, Inc.	Inhibitors of hcv ns5a
WO2010094977A1 (en)	2009-02-23	2010-08-26	Arrow Therapeutics Limited	Novel biphenyl compounds useful for the treatment of hepatitis c
RU2544010C2 (ru)	2009-02-27	2015-03-10	Энанта Фармасьютикалс, Инк.	Ингибиторы вируса гепатита с
CA2756255A1 (en)	2009-03-27	2010-09-30	Presidio Pharmaceuticals, Inc.	Substituted bicyclic hcv inhibitors
AU2010229833B2 (en)	2009-03-27	2014-03-13	Merck Sharp & Dohme Llc	Inhibitors of hepatitis C virus replication
BRPI1012282A2 (pt)	2009-03-27	2015-09-22	Presidio Pharmaceuticals Inc	inibidores de anel fundidos da hepatite c.
TWI476190B (zh)	2009-03-30	2015-03-11	必治妥美雅史谷比公司	Ｃ型肝炎病毒抑制劑
US8796466B2 (en)	2009-03-30	2014-08-05	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US8143414B2 (en)	2009-04-13	2012-03-27	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
RU2541571C2 (ru)	2009-04-15	2015-02-20	Эббви Инк.	Противовирусные соединения
RU2528231C2 (ru)	2009-04-24	2014-09-10	Тиботек Фармасьютикалз	Диариловые эфиры
US9139569B2 (en)	2009-05-12	2015-09-22	Merck Sharp & Dohme Corp.	Fused tricyclic aryl compounds useful for the treatment of viral diseases
MX360800B (es)	2009-05-13	2018-11-16	Gilead Pharmasset Llc Star	Compuestos antivirales.
US8980920B2 (en)	2009-05-29	2015-03-17	Merck Sharp & Dohme Corp.	Antiviral compounds of three linked aryl moieties to treat diseases such as hepatitis C
US8211928B2 (en)	2009-05-29	2012-07-03	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
CA2762885A1 (en)	2009-05-29	2010-12-02	Schering Corporation	Antiviral compounds composed of three aligned aryl moieties to treat diseases such as hepatitis c
US8138215B2 (en)	2009-05-29	2012-03-20	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
AR077060A1 (es)	2009-06-11	2011-07-27	Abbott Lab	Compuestos antivirales
WO2010148006A1 (en)	2009-06-16	2010-12-23	Enanta Pharmaceuticals, Inc.	Hepatitis c virus inhibitors
WO2011004276A1 (en)	2009-07-06	2011-01-13	Pfizer Limited	Hepatitis c virus inhibitors
MX2012000695A (es)	2009-07-16	2012-06-12	Vertex Pharma	Análogos de bencimidazol para el tratamiento o la prevención de infecciones por flavivirus.
WO2011015657A1 (en)	2009-08-07	2011-02-10	Tibotec Pharmaceuticals	Phenyl ethynyl derivatives as hepatitis c virus inhibitors
WO2011015658A1 (en)	2009-08-07	2011-02-10	Tibotec Pharmaceuticals	Bis-benzimidazole derivatives as hepatitis c virus inhibitors
RU2012112824A (ru)	2009-09-03	2013-10-10	Тиботек Фармасьютикалз	Производные бис-бензимидазола
CN102480971B (zh)	2009-09-04	2014-11-26	杨森制药公司	化合物
EP2475254A4 (en)	2009-09-11	2013-05-22	Enanta Pharm Inc	HEPATITIS C-VIRUS HEMMER
EP2475256A4 (en)	2009-09-11	2013-06-05	Enanta Pharm Inc	HEPATITIS C-VIRUS HEMMER
US8415374B2 (en)	2009-10-12	2013-04-09	Bristol-Myers Squibb Company	Combinations of hepatitis C virus inhibitors
WO2011050146A1 (en)	2009-10-23	2011-04-28	Glaxosmithkline Llc	Chemical compounds
UA108211C2 (uk)	2009-11-04	2015-04-10	Янссен Рід Айрленд	Бензімідазолімідазольні похідні
US20110269956A1 (en)	2009-11-11	2011-11-03	Bristol-Myers Squibb Company	Hepatitis C Virus Inhibitors
US20110274648A1 (en)	2009-11-11	2011-11-10	Bristol-Myers Squibb Company	Hepatitis C Virus Inhibitors
US20110281910A1 (en)	2009-11-12	2011-11-17	Bristol-Myers Squibb Company	Hepatitis C Virus Inhibitors
US20120276047A1 (en)	2009-11-25	2012-11-01	Rosenblum Stuart B	Fused tricyclic compounds and derivatives thereof useful for the treatment of viral diseases
TWI429645B (en)	2009-12-04	2014-03-11		Proline derivatives
US8653070B2 (en)	2009-12-14	2014-02-18	Enanta Pharmaceuticals, Inc.	Hepatitis C virus inhibitors
US8377980B2 (en)	2009-12-16	2013-02-19	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
KR20120118008A (ko)	2009-12-18	2012-10-25	아이데닉스 파마슈티칼스, 인코포레이티드	5,5-융합 아릴렌 또는 헤테로아릴렌 간염 ｃ 바이러스 억제제
CN102791687B (zh)	2009-12-18	2015-02-11	北京凯因科技股份有限公司	C型肝炎病毒复制的新型抑制剂
WO2011087740A1 (en)	2009-12-22	2011-07-21	Schering Corporation	Fused tricyclic compounds and methods of use thereof for the treatment of viral diseases
WO2011079327A1 (en)	2009-12-24	2011-06-30	Vertex Pharmaceuticals Incorporated	Analogues for the treatment or prevention of flavivirus infections
WO2011091446A1 (en)	2010-01-22	2011-07-28	Glaxosmithkline Llc	Chemical compounds
JP2013518060A (ja)	2010-01-25	2013-05-20	エナンタファーマシューティカルズインコーポレイテッド	Ｃ型肝炎ウイルス阻害剤
EP2528926A4 (en)	2010-01-28	2013-06-19	Boehringer Ingelheim Int	HEPATITIS C INHIBITOR COMPOUNDS

2010
- 2010-03-26 TW TW099109167A patent/TW201038559A/zh unknown
- 2010-04-05 US US12/754,169 patent/US8143301B2/en active Active
- 2010-04-06 AU AU2010234608A patent/AU2010234608B2/en not_active Ceased
- 2010-04-06 PE PE2011001706A patent/PE20120533A1/es not_active Application Discontinuation
- 2010-04-06 CA CA2757963A patent/CA2757963A1/en not_active Abandoned
- 2010-04-06 EA EA201171208A patent/EA018793B1/ru not_active IP Right Cessation
- 2010-04-06 WO PCT/US2010/030032 patent/WO2010117977A1/en not_active Ceased
- 2010-04-06 CN CN201080025741.5A patent/CN102803249B/zh not_active Expired - Fee Related
- 2010-04-06 ES ES10714127.7T patent/ES2502667T3/es active Active
- 2010-04-06 SG SG2011069861A patent/SG174582A1/en unknown
- 2010-04-06 MY MYPI2011006293A patent/MY152971A/en unknown
- 2010-04-06 JP JP2012504758A patent/JP5558556B2/ja not_active Expired - Fee Related
- 2010-04-06 BR BRPI1010506A patent/BRPI1010506A2/pt not_active IP Right Cessation
- 2010-04-06 KR KR1020117026556A patent/KR20120133366A/ko not_active Ceased
- 2010-04-06 MX MX2011010478A patent/MX2011010478A/es active IP Right Grant
- 2010-04-06 NZ NZ595186A patent/NZ595186A/xx not_active IP Right Cessation
- 2010-04-06 EP EP10714127.7A patent/EP2417126B1/en not_active Not-in-force
- 2010-04-09 AR ARP100101218A patent/AR076274A1/es unknown
2011
- 2011-09-11 IL IL215095A patent/IL215095A0/en not_active IP Right Cessation
- 2011-09-28 ZA ZA2011/07095A patent/ZA201107095B/en unknown
- 2011-10-06 CO CO11132299A patent/CO6440581A2/es active IP Right Grant
- 2011-10-07 CL CL2011002524A patent/CL2011002524A1/es unknown

Also Published As

Publication number	Publication date
CL2011002524A1 (es)	2012-03-23
MY152971A (en)	2014-12-15
EA018793B1 (ru)	2013-10-30
KR20120133366A (ko)	2012-12-10
ZA201107095B (en)	2013-03-27
EP2417126A1 (en)	2012-02-15
EP2417126B1 (en)	2014-07-02
AR076274A1 (es)	2011-06-01
PE20120533A1 (es)	2012-05-09
WO2010117977A1 (en)	2010-10-14
CN102803249B (zh)	2014-09-10
CA2757963A1 (en)	2010-10-14
AU2010234608A1 (en)	2011-10-06
US8143301B2 (en)	2012-03-27
IL215095A0 (en)	2011-11-30
BRPI1010506A2 (pt)	2016-07-26
CN102803249A (zh)	2012-11-28
AU2010234608B2 (en)	2016-04-14
SG174582A1 (en)	2011-10-28
US20100260708A1 (en)	2010-10-14
MX2011010478A (es)	2011-10-17
JP5558556B2 (ja)	2014-07-23
ES2502667T3 (es)	2014-10-03
NZ595186A (en)	2013-06-28
EA201171208A1 (ru)	2012-05-30
CO6440581A2 (es)	2012-05-15
JP2012523415A (ja)	2012-10-04

Publication	Publication Date	Title
TW201038559A (en)	2010-11-01	Hepatitis C virus inhibitors
US8138215B2 (en)	2012-03-20	Hepatitis C virus inhibitors
TWI476190B (zh)	2015-03-11	Ｃ型肝炎病毒抑制劑
CN102459281B (zh)	2015-03-11	丙型肝炎病毒抑制剂
TWI438200B (zh)	2014-05-21	Ｃ型肝炎病毒抑制劑
CA2780790C (en)	2017-10-17	Hepatitis c virus inhibitors
TWI487702B (zh)	2015-06-11	Ｃ型肝炎病毒抑制劑
ES2386590T3 (es)	2012-08-23	Inhibidores del virus de la hepatitis C
CN102459250B (zh)	2015-05-06	丙型肝炎病毒抑制剂
TW201121955A (en)	2011-07-01	Hepatitis C virus inhibitors
TW200938192A (en)	2009-09-16	Hepatitis C virus inhibitors
TW200938191A (en)	2009-09-16	Hepatitis C virus inhibitors
TW201038558A (en)	2010-11-01	Hepatitis C virus inhibitors